Diastereoselective total synthesis of (+)-13-stemarene by fourth generation methods: a formal total synthesis of (+)-18-deoxystemarin

J Org Chem. 2011 Aug 19;76(16):6871-6. doi: 10.1021/jo200945s. Epub 2011 Jul 19.

Abstract

The problem of constructing diastereoselectively the C/D ring system of stemarane diterpenes from a bicyclo[2.2.2]octane intermediate was solved resulting in very simple synthesis of (+)-13-stemarene 1. The obtaining of the latter represents also a formal synthesis of (+)-18-deoxystemarin 2. In the key step, the epimeric mixture 10, dissolved in toluene, was converted by the action of TsOH into (+)-stemar-13-en-15-one 28.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • (+)-13-stemarene
  • (+)-18-deoxystemarin
  • Diterpenes